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1.
Summary 3,6-Dichloro- and 3,6-dibromo-8-quinolinols were prepared by direct halogenation of 8-nitroquinoline by N-halosuccinimide in acetic acid or by halogenation of the corresponding 6-halo-8-nitroquinoline prepared via aSkraup reaction. The nitro group was reduced to amino and the amine was hydrolyzed to the phenol in 70% sulfuric acid at 220°C. The fungitoxicity of 3,6-dichloro- and 3,6-dibromo-8-quinolinols, as well as intermediates in their preparation, againstAspergillus niger, Aspergillus oryzae, Myrothecium verrucaria, Trichoderma viride, andMucor cirinelloides was determined. 3,6-dichloro-8-quinolinol is the most fungitoxic analogue of this class of compounds observed to date.
Herstellung und Fungitoxizität von 3,6-Dichlor- und 3,6-Dibrom-8-chinolinen
Zusammenfassung 3,6-Dichlor- und 3,6-Dibrom-8-chinoline wurden durch direkte Halogenierung von 8-Nitrochinolin mit N-Halogensuccinimid in Essigsäure oder durch Halogenierung der entsprechenden nachSkraup synthetisierten 6-Halogen-8-nitrochinoline hergestellt. Die Nitrogruppe wurde zum Amin reduziert und die Aminofunktion in 70% iger Schwefelsäure bei 220°C zum Phenol hydrolysiert. Die Fungitoxizität der 3,6-Dichlor- und 3,6-Dibrom-8-chinoline und jene der bei ihrer Herstellung auftretenden Zwischenstufen gegenAspergillus niger, Aspergillus oryzae, Myrothecium verrucaria, Trichoderma viride undMucor cirinelloides wurde bestimmt. 3,6-Dichlor-8-chinolin ist der derzeit stärkste bekannte fungitoxische Vertreter dieser Substanzklasse.相似文献
2.
Herman Gershon Donald D. Clarke John J. McMahon 《Monatshefte für Chemie / Chemical Monthly》2003,134(8):1099-1104
Summary. Polyhalo-8-quinolinols with chlorine or bromine in position 4 were not stable in DMSO or DMF. The degradation product from 4,5-dichloro-8-quinolinol was 5-chloro-4,8-quinolindiol and the major product from 4,5-dibromo-8-quinolinol was 3,5-dibromo-4,8-quinolindiol. 4,5,7-Trichloro- and 4,5,7-tribromo-8-quinolinols yielded similar hydrolytic products, and for the bromo compound, a rebrominated product in DMSO. In DMF rebromination did not occur. In pyridine-d5 these reactions did not take place, indicating a special ability of DMSO and DMF to cause such hydrolysis at position 4 of 4-halo-8-quinolinols.Received December 13, 2002; accepted January 7, 2003
Published online June 23, 2003 相似文献
3.
A. Aykut İkizler Haydar Yüksek Şule Bahçeci 《Monatshefte für Chemie / Chemical Monthly》1992,123(1-2):191-198
Summary The proton magnetic resonance spectra of 12 azoles were measured in neutral and acidic solvents. The protonation shifts observed by comparison of the spectra inDMSO-d
6 andTFA were attributed to an amidinium type resonance of the resulting cations. The synthesis and characterization of the azoles are also discussed.
1H-NMR-Spektren einiger Ditriazolyle und Ditriazolylalkane
Zusammenfassung Es wurden die1H-NMR-Spektren von 12 Azol-Verbindungen in neutralem (DMSO-d 6) und azidischem (TFA) Lösungsmittel gemessen und die chemischen Verschiebungswerte verglichen. Der Unterschied beider Werte beruht höchstwahrscheinlich auf einer Amidinium-Typ Resonanz der im azidischen Bereich entstandenen Kationen. Im Rahmen dieser Arbeit wurden 12 Azol-Verbindungen synthetisiert und beschrieben.相似文献
4.
Herman Gershon Donald D. Clarke John J. McMahon Muriel Gershon 《Monatshefte für Chemie / Chemical Monthly》2001,132(7):833-838
Summary. 2,5-, 3,5-, 3,6-, 3,7-, 4,5-, 5,6-, 5,7-, and 6,7-dibromo-8-quinolinols were prepared and tested against six fungi (Aspergillus niger, Aspergillus oryzae, Myrothecium verrucaria, Trichoderma viride, Mucor cirinelloides, and Trichophyton mentagrophytes) in Sabouraud dextrose broth. Most of the compounds were strongly antifungal, inhibiting five of the fungi below 1μg/cm3, but were somewhat less fungitoxic than the corresponding chloro analogues. M. cirinelloides was not inhibited by any of the compounds except 4,5-dibromo-8-quinolinol. This high level of fungitoxicity is attributed
to intramolecular synergism.
Received December 28, 2000. Accepted (revised) February 3, 2001 相似文献
5.
Summary The halogenation of derivatives of 2-aminophenol with N-chloro- and N-bromosuccinimides at ambient temperatures in acetic acid was studied. With the necessary compounds available, a reexamination of the thermolytic rearrangement of 2-halophenyl azides to 2-aminophenols and other products was undertaken. It is certain that the rearrangement of 4-halophenyl azides to 2-aminophenols occurs but the products identified in this study differ significantly from those reported previously by Suschitzky et al. (1963, 1966).
Neuuntersuchung der thermolytischen Umlagerung von 4-Halogenphenylaziden zu 2-Aminophenolen und anderen Produkten
Zusammenfassung Es wurde die Halogenierung von 2-Aminophenol-Derivaten mit N-Chlor- und N-Bromsuccinimid bei Raumtemperatur in Essigsäure untersucht. Mit den zur Verfügung stehenden Verbindungen konnte eine Neuuntersuchung der thermolytischen Umlagerung von 4-Halogenphenylaziden zu 2-Aminophenolen und anderen Produkten unternommen werden. Diese Umlagerung findet sicherlich statt, allerdings differieren die dabei beobachteten Produkte signifikant von denen, die Suschitzky et al. 1963 und 1966 beschrieben.相似文献
6.
Summary An antifungal study againstAspergillus niger,A. oryzae,Myrothecium verrucaria, andTrichoderma viride in Yeast Nitrogen Base supplemented with 1%D-glucose and 0.088%L-asparagine was carried out using 8-quinolinol and 3-, 5-, 6-, 7-, 3,6-, and 5,7-chlorinated and brominated-8-quinolinols. Binary mixtures of 3- and 6-halo- and 5- and 7-halo-8-quinolinols were intermolecularly synergistic. MICs of the monohalo synergistic mixtures admixed with a MIC of the corresponding dihalo-8-quinolinols were not synergistic. The dihalo-8-quinolinols with substituents in positions corresponding to those of the synergistic binary mixtures appeared to attack the same sites of action as the binary pairs. The enhanced activities of 3,6- and 5,7-dichloro-8-quinolinols and 3,6- and 5,7-dibromo-8-quinolinols are believed to be due to intramolecular synergism. The greater fungitoxicity of 5-, 6-, and 7-monohalo-8-quinolinols over 8-quinolinol can also be explained as due to intramolecular synergism. 3,6-Dihalo- and 5,7-dihalo-8-quinolinols formed synergistic pairs of compounds.
Intramolekularer Synergismus als Erklärung für die erhöhte Fungitoxizität von halogenierten 8-Chinolinolen
Zusammenfassung 8-Chinolinol und verschiedene halogenierte 8-Chinolinole wurden auf ihre Fungitoxizität gegenüberAspergillus niger,A. oryzae,Myrothecium verrucaria undTrichoderma viride untersucht. Binäre Mischungen von 3- und 6-Halogen- bzw. 5- und 7-Halogen-8-chinolinol zeigten intermolekularen Synergismus, während bei Mischungen von mono- und dihalogenierten 8-Chinolinolen kein entsprechender Effekt beobachtet werden konnte. Die erhöhte Aktivität von 3,6-und 5,7-Dichlor-8-chinolinol und 3,6- und 5,7-Dibrom-8-chinolinol wird durch intramolekularen Synergismus erklärt, desgleichen die höhere Aktivität monohalogenierter 8-Chinolinole gegenüber 8-Chinolinol. 3,6-Dihalogenierte und 5,7-dihalogenierte 8-Chinolinole bilden synergistische Paare.相似文献
7.
Herman Gershon Donald D. Clarke Muriel Gershon 《Monatshefte für Chemie / Chemical Monthly》2001,132(9):1075-1080
Summary. 3,5,6-, 3,5,7-, 4,5,7-, and 5,6,7-trichloro- and -tribromo-8-quinolinols as well as 3,5,6,7-tetrachloro- and -tetrabromo-8-quinolinols
were prepared and tested against six fungi (Aspergillus niger, Aspergillus oryzae, Myrothecium verrucaria, Trichoderma viride, Mucor cirinelloides, and Trichophyton mentagrophytes) in Sabouraud dextrose broth. The compounds strongly inhibit five fungi but not M. cirinelloides. They are less active than the related dichloro-8-quinolinols which is attributed to steric hindrance.
Received April 3, 2001. Accepted April 10, 2001 相似文献
8.
The complexes of niobium(V) with 2-phenyl-1,1,3,3-tetraacetylpropane and 2-phenyl-1,3-diacetyl-1,3-dibenzoylpropane were investigated by IR, UV,1H-NMR, and magnetic measurements. Together with analytical data and determination of molecular weights a trimeric structure is proposed for both 1:1 complexes.
Komplexierung von Niob(V) mit einigen Bis(-diketonen)
Zusammenfassung Es wurden die Komplexe von Niob(V) mit 2-Phenyl-1,1,3,3-tetraacetylpropan und 2-Phenyl-1,3-diacetyl-1,3-dibenzoylpropan untersucht. IR-, UV- und1H-NMR-Spektren sowie magnetische Messungen zusammen mit analytischen Daten und Molekulargewichtsbestimmungen ergaben für beide 1:1 Komplexe eine trimere Struktur.相似文献
9.
Starting from optically active 5,5-dimethyl, diethyl, and 5-ethyl-5-methyl-2,2-spirobiindane as well as from 5-ethyl-spirobiindane-5-carboxylic ester of known enantiomeric purity and configuration 75 mono to polysubstituted 2,2-spirobiindanes have been prepared. Amongst these are several compounds with rings anellated in the 6,7 (and 6, 7) positions, especially a spirohydrocarbon4 x with orthogonal naphthalene units the circular dichroism of which is reported and discussed.Several mono and disubstituted 5-methyl and ethylindanes (1,2) have been prepared as models for synthetic transformations in the spirobiindane series.From the molar rotations of symmetrically diacylated 5,5-dimethyl and diethyl spirobiindanes (4a, 7b, 7c) empirical ligand parameters for acetyl and methoxycarbonyl were determined which gave much better results in the calculation of the rotations of appropriate spirobiindanes (with the shortened polynomal Ansatz) than the -values deduced previously from 5,5-disubstituted spirobiindanes. The significance of these results is briefly discussed.
10. Mitt.:Neudeck, H., Schlögl, K., Angew. Chem.92, 318 (1980), Intern. Ed. Engl.19, 308 (1980). 相似文献
10.
Afonin A. V. Kuznetsova S. Yu. Ushakov I. A. Petrova O. V. Voronov V. K. Mikhaleva A. I. 《Russian Chemical Bulletin》2001,50(3):551-553
The reactions of 2-, 3-, and 4-(1-vinylpyrrol-2-yl)pyridines with methyl iodide afford the corresponding quaternary salts. Analysis of their 1H and 13C NMR spectra showed that the quaternization of the nitrogen atom considerably enhances the -acceptor effect of the pyridine ring on the pyrrole ring and on the vinyl group. 1-Methyl-2-(1-vinylpyrrol-2-yl)pyridinium iodide contains no weak intramolecular C--H...N hydrogen bond present in the starting compound. 相似文献
11.
Rafat Milad Mohareb 《Monatshefte für Chemie / Chemical Monthly》1992,123(4):341-347
Summary The enamino nitriles1 and2 react with phenyl isothiocyanate followed by cyclization with -haloketones3 and10 to afford in each case the thiazole5, thiophene11 and the thieno[2,3-b]pyridine derivatives19 and21. Chemical and spectroscopic evidences for the structures of the new compounds are described.
Phenylisothiocyanate in der Heterocyclensynthese: Neue Synthesen für Thiazol-, Thieno [2,3-b]pyridin-, Thiophen- und Thieno[3,2-c]pyridazin-Derivate
Zusammenfassung Die Enamin-nitrile1 und2 ergaben nach Reaktion mit Phenylisothiocyanaten und nachfolgender Cyclisierung mit -Halogenketonen3 und10 die entsprechenden Thiazole5, die Thiophene11 und die Thieno[2,3-b]pyridine19 und21. Chemische und spektroskopische Untersuchungen wurden als Strukturbeweise für die neuen Verbindungen herangezogen.相似文献
12.
《Journal of Coordination Chemistry》2012,65(8):1293-1301
Interaction of 1-(2-pyridylazo)-2-naphthol (PAN) with [Mo(CO)6] in air resulted in formation of the tricarbonyl oxo-complex [Mo(O)(CO)3(PAN)], 1. The dicarbonyl complex [Ru(CO)2(PAN)], 3, was obtained from the reaction of [Ru3(CO)12] with PAN. In presence of triphenyl phosphine (PPh3), the reaction of PAN with either Mo(CO)6 or Ru3(CO)12 gave [Mo(CO)3(PAN)(PPh3)], 2, and [Ru(CO)2(PAN)(PPh3)], 4. All the complexes were characterized by elemental analysis, mass spectrometry, IR, and NMR spectroscopy. The thermal properties of the complexes were also investigated by thermogravimetry. 相似文献
13.
《Journal of Coordination Chemistry》2012,65(19):3471-3482
The interactions of yttrium chloride, zirconium chloride, and uranium nitrate with sparfloxacin (SPAR) in ethanol, methanol, and acetone were studied. The isolated solid complexes were characterized by elemental analysis, infrared, 1H-NMR and electronic spectra, and thermogravimetric analysis. The results support the formation of [Y(SPAR)2Cl2]Cl ? 12H2O, [ZrO(SPAR)2Cl]Cl ? 15H2O, and [UO2(SPAR)3](NO3)2 ? 5H2O. Infrared spectra of the isolated solid complexes indicate that SPAR is bidentate through the ring carbonyl oxygen and one oxygen of carboxylate. The calculated bond length and force constant, F(U=O), in the uranyl complex are 1.747 Å and 655.29 Nm?1, respectively. The antimicrobial activities of the ligand and metal complexes have been tested against bacteria Staphylococcus aureus (S. aureus), Escherichia coli (E. coli) and Pseudomonas aeruginosa (P. aeruginosa) and fungi Penicillium rotatum (P. rotatum) and Trichoderma sp., showing that the complexes exhibit higher antibacterial activity than SPAR. 相似文献
14.
15.
《Journal of Coordination Chemistry》2012,65(24):4225-4243
Six complexes, [VO(L1-H)2]?·?5H2O (1), [VO(OH)(L2,3?H)(H2O)]?·?H2O (2,3), [VO(OH)(L4,5?H)(H2O)]?·?H2O (4,5), [VO(OH)(L6?H)(H2O)]?·?H2O (6), were prepared by reacting different derivatives of 5-phenylazo-6-aminouracil ligands with VOSO4?·?5H2O. The infrared and 1H NMR spectra of the complexes have been assigned. Thermogravimetric analyses (TG, DTG) were also carried out. The data agree quite well with the proposed structures and show that the complexes were finally decomposed to the corresponding divanadium pentoxide. The ligands and their vanadyl complexes were screened for antimicrobial activities by the agar-well diffusion technique using DMSO as solvent. The minimum inhibitory concentration (MIC) values for 1–4 and 6 were calculated at 30°C for 24–48?h. The activity data show that the complexes are more potent antimicrobials than the parent ligands. 相似文献
16.
Abstract With a 1:1 and a 2:1 host-guest stoichiometry, α-cyclodextrin (α-CD) forms inclusion complexes with 2-chloronaphthalene. From simulations concerning observed chemical-shift differences (Δδobs) of proton signals of 2-chloronaphthalene, intrinsic Δδ values are estimated for all the guest protons in the 1:1 and 2:1 inclusion complexes. The intrinsic Δδ values indicate that α-CD first binds to a part of a naphthalene ring bearing a C1 atom to form the 1:1 inclusion complex. In the 1:1 and 2:1 inclusion complexes, the symmetry axes of α-CD are tilted approximately 30° relative to a naphthalene longitudinal axis. In the 2:1 inclusion complex, the association through hydrogen bonding most likely occurs between two α-CD molecules whose symmetry axes are laterally shifted. 相似文献
17.
Vaggelis Hondrellis Themistoclis Kabanos Spyros P. Perlepes John M. Tsangaris 《Monatshefte für Chemie / Chemical Monthly》1988,119(10):1091-1101
New complexes of the formulaeM(fur)2·2H2O (M = Mn, Cu, Zn),M(fur)2·3H2O (M = Co, Ni, Cd), Hg2(fur)3Cl2·2H2O, Pd(fur)Cl·H2O and Rh(fur)3·3H2O, wherefurH = 4-chloro-N-(2-furfuryl)-5-sulfamoylanthranilic acid, have been prepared and characterized by conductivity measurements, X-ray powder patterns, thermal methods, effective magnetic moments as well as by IR, ligand field,1H-NMR and ESR spectroscopic studies. The anionfur
– shows a chelated bidentate O(carboxylato), N(imino)-coordinating behaviour.
Metallkomplexe der diuretischen Droge Furosemid
Zusammenfassung Neue Komplexe der Verbindungen:M(fur)2·2H2O (M = Mn, Cu, Zn),M(fur)2·3H2O (M = Co, Ni, Cd), Hg2(fur)3Cl2·2H2O, Pd(fur)Cl·H2O und Rh(fur)3·3H2O, wobeifurH 4-chlor-N-(2-furfuryl)-5-sulfamoylanthanilsäure ist, wurden dargestellt. Die Komplexe wurden durch Leitfähigkeitsmessungen, Röntgen-Pulver-Aufnahmen, thermogravimetrische Analysen, Messungen des effektiven magnetischen Dipolemomentes sowie durch spektroskopische Untersuchungen (IR,1H-NMR und ESR) charakterisiert. Das Anionfur – zeigt das Verhalten einer Chelat-bidentat-O(carboxylato),N(imino)-Koordination.相似文献
18.
Rafael López-Garzón Dolores Gutierrez-Valero Manuel Nogueras-Montiel Adolfo Sánchez-Rodrigo Cristóbal Valenzuela-Calahorro 《Monatshefte für Chemie / Chemical Monthly》1986,117(8-9):905-920
Six Pd(II) and Au(III) complexes of 4-glycopyranosylamino-5-nitroso-6-oxo-pyrimidine derivatives were prepared. On the basis of their1H-NMR and IR spectra, it has been found that the coordination sites are the 5-nitroso and the 6-oxo substituents. Likewise, the thermal behaviour of the complexes has also been studied.
Komplexe des Pd(II) und Au(III) mit einigen Derivaten des 4-Glycopyranosylamino-5-nitroso-6-oxo-pyrimidins
Zusammenfassung Sechs Pd(II)- und Au(III)-Komplexe mit 4-Glycopyranosylamino-5-nitroso-6-oxo-pyrimidin-Derivaten wurden hergestellt. Auf der Basis ihrer1H-NMR und IR-Spektren wurde herausgefunden, daß die Substituenten 5-nitroso und 6-oxo die Koordinationsstellen sind. Das thermische Verhalten der Komplexe wurde ebenfalls untersucht.相似文献
19.
N. Raman V. Muthuraj S. Ravichandran A. Kulandaisamy 《Journal of Chemical Sciences》2003,115(3):161-167
Neutral tetradentate N2O2 type complexes of Cu(II), Ni(II), Co(II) and Zn(II) have been synthesised using the Schiff base formed by the condensation
of acetylacetone andp-anisidine. Microanalysis, molar conductance, magnetic susceptibility, IR, UV-Vis,1 H NMR, CV and EPR studies have been carried out to determine the structure of the complexes. From the data, it is found that
all the complexes possess square-planar geometry. The EPR spectrum of the copper complex in DMSO at 300 K and 77 K was recorded
and its salient features are reported. All the title complexes were screened for antimicrobial activity by the well diffusion
technique using DMSO as solvent. The minimum inhibitory concentration (MIC) values were calculated at 37°C for a period of
24 h. It has been found that all the complexes are antimicrobially active and show higher activity than the free ligand. 相似文献
20.
A Stability Indicating Proton NMR Spectroscopic Assay Method for Succinylcholine Chloride Injections
《Analytical letters》2012,45(17):2183-2194
Abstract A simple, accurate, and specific -1H-NMR spectroscopic method is presented for the assay of succinylcholine chloride injections. After freeze-drying the sample solution, a mixture of the residue with acetamide, serving as the internal standard, is dissolved in deuterium oxide, and the spectrum of the solution is recorded. The quantity of drug in the dosage form is calculated from the integral values for the resonance signals at ca. 2.01 ppm (acetamide) and ca. 3.27 ppm (succinylcholine chloride). The mean ± SD recovery value from synthetic formulations was 99.93 ± 0.60% (n = 10), with a corresponding CV of 0.60%. Assay values for a group of 10 commercial samples ranged from 86.1 to 100.7 (mean = 98.01)% of declared. Injection additives such as methyl paraben and benzyl alcohol did not interfere with the assays. The proposed method will also permit the simultaneous monitoring of the hydrolytic degradation of succinylcholine to its ester components. 相似文献